Synthesis and structural features of new calix[4]resorcinols with anthracene- and pyrene-ended isoxazole-containing fragments

• Published in: Mendeleev communications Vol. 34; no. 3; pp. 392 - 395
• Main Authors: Mironova (Knyazeva), Irina R., Romashov, Nikita P., Syakaev, Victor V., Gerasimova, Daria P., Lodochnikova, Olga A., Burilov, Alexander R.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-05-2024
• Subjects: anthracene; calixresorcinols; condensation; diastereoisomer; isoxazole; pyrene; anthracene; condensation; diastereoisomer; isoxazole; pyrene; calixresorcinols
• ISSN: 0959-9436
• DOI: 10.1016/j.mencom.2024.04.025

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Reactions between 4-(propargyloxy)benzaldehyde with anthracene-9-carbaldehyde oxime or pyrene-1-carbaldehyde oxime in the presence of chloramine T in ethanol lead to new isoxazole-containing derivatives of benzaldehyde. The subsequent acid-catalyzed condensation of these compounds with 2-methylresorcinol in chloroform/trifluoroacetic acid mixtures affords novel calix[4]resorcinols with anthaceneand pyrene-ended isoxazole-containing fragments as all–cis (rccc) and cis–trans–trans (rctt) diastereoisomers, their ratios being dependent on the CF3CO2H percentage in the medium. The crystal structures of pyrene-ended isoxazole-containing benzaldehyde and corresponding calix[4]resorcinol rctt isomer have been established by single crystal X-ray diffraction.